Be Your Own Best Tour Guide in Provincetown

Sponsored by the Provincetown Office of Tourism

Before reaching their more famous landing spot more than 400 years ago, the Pilgrims aboard the Mayflower stumbled upon the tip of Cape Cod — specifically, they first arrived in what would become Provincetown, Massachusetts (an Outer Cape bragging point). The Provincetown of today, though, is a little less uncharted.

Boutique shopping, art galleries, fine dining and wallet-friendly dining, and an abundance of natural beauty fill this ever-changing coastal hamlet that’s home to fishermen, creatives, and the LGBTQIA+ community alike.

Tourists and locals pack Commercial Street, the main thoroughfare, during the high summer season. But late spring and early summer are terrific times to enjoy the charms of this historic enclave before the bigger crowds arrive by car, ferry, and Cape Air.

Provincetown’s compact size makes it ideal for exploring on foot or by bike. You can download tour maps of the Provincetown Cultural District and local historic sites online, or simply put on your best walking shoes and let your own interests (and appetites) guide you through the bustling streets and beautiful dunes.

And don’t worry: As the following two-day itinerary makes clear, there’s something for everyone in Ptown.

Day 1: Downtown Provincetown Walk-Around

No matter where you stay in Ptown, fueling up for your first day is a cinch. Joe Coffee and Kohi Coffee Co. are hubs of the local java scene, and their central locations in the West End make them great spots to start your strolling.

With a Frozen Joe espresso or perhaps Kohi’s golden turmeric latte in hand, make your way east up Commercial Street. Pop left down a small lane called Masonic Place, and you’ll see a white clapboard building with a covered porch — that’s the Atlantic House, one of the nation’s oldest continuously running gay bars (and livelier in the later hours than daytime).

Back on Commercial Street, you can pick up a beach read or two at the Provincetown Bookshop, and make note of its next-door neighbor, The Canteen, as a future lunch spot. It’s well worth returning for a lobster roll in the backyard of this casual-dining favorite.

Keep strolling east, and on the left you’ll encounter the first of many popular Ptown art galleries, such as Cortile Gallery and Thanassi Gallery (with its can’t-miss-them turquoise canvases in the front garden). On the right is the perennially popular Crown & Anchor, which offers everything from overnight accommodations to brunch to nightlife and dancing.

One block onward is the Provincetown Town Hall, a grand Victorian building that lords over Commercial Street but also provides an inviting outdoor space where people can relax on benches, and maybe take in some entertainment from a singer or guitarist strumming out front. Inside, nationally known performers often grace the stage in the spacious auditorium.

Behind Town Hall, cross Bradford Street to reach a green-framed incline elevator. From April to early November, this will whisk you up to the Pilgrim Monument & Provincetown Museum, where you can learn all about Ptown’s history going back to the native Wampanoag peoples. Don’t miss the chance to climb up the 116 steps and 60 ramps to the top of the monument for the best view of town.

Worked up an appetite? Back on Bradford Street you’ll find Provincetown Brewing Co., known for its local brews, delicious sandwiches, and community spirit, or return to Commercial Street for a quick sugar hit at either Cabot’s Candy or the Penney Patch.

The stretch of Commercial between Ryder and Standish streets is chockablock with eateries and boutique shopping, from funky clothes and gifts at Shop Therapy to the iconic casualwear of The Black Dog. The Provincetown Portuguese Bakery is a must-stop for malassadas (a Portuguese spin on the doughnut) and chorizo-and-cheese croissants. Across the street, The Mayflower offers an affordable mix of Portuguese, Italian, seafood, and comfort food.

Crossing Standish Street brings you into the East End of Provincetown, where you’ll find more art galleries and shops — plus an unusual reason to stop into the local library. Along with the expected shelves of books and magazines, the Provincetown Public Library also features more than two dozen works of art and a half-scale model of the Rose Dorothea, a local schooner that won the famed Lipton Cup yacht race in 1907.

Keep your eyes peeled after leaving the library for the cobblestone steps leading down to the waterfront Harbor Lounge and, a little farther along Commercial, 361 Coffee & Espresso Bar — either of these would be a great spot for cocktail hour, later on. But you don’t have to wait to indulge in a bit of retail therapy at places like Room 68, featuring high-end art and statement home décor; Womencrafts, a showcase for female authors, artists, and musicians; and Utilities, a dangerously addictive shop for all kinds of housewares and host gifts.

Make sure to leave ample time in the East End for exploring a must-see Ptown institution, the Provincetown Art Association and Museum (PAAM), located at Commercial and Bangs streets. Founded in 1914, this cultural treasure trove is known for its permanent collection of Outer Cape artists like Edward Hopper and Blanche Lazzell as well as its vibrant lineup of exhibitions and events.

After you’ve gotten your fill of art, it’s time to think about dinner plans. Across the street from PAAM, the gourmet market Angel Foods has on-the-go fare, from snacks and sandwiches to entrees. Also close by are two of Ptown’s longtime year-round restaurants, Ciro & Sal’s and The Mews Restaurant & Café. The former serves Italian in a rustic, wood-beamed dining room (who doesn’t love a puttanesca with a pirate-ship vibe?), while the latter features a wide-ranging menu of comfort food in its temporary digs at the Waterford Inn, as its own waterfront location undergoes repairs (through summer 2024).

Day 2: Two Wheels, No Waiting

Coffee isn’t the only thing worth grabbing this morning — to broaden your explorations, you’ll want to pick up a bike, too. Ptown Bikes and Gale Force Bikes are the best options for those staying in the West End, while Arnold’s Bike Shop and Provincetown Bike Rentals are convenient for those staying in the center of town or in the East End.

If you’re getting a late start, that’s OK: Perry’s Fine Wine & Liquors doesn’t open till noon (a “NOPE” sign in the window is your clue you’ve arrived too early). Once inside the specialty food and wine store, you can collect upscale snacks like black truffle potato chips and artisan cheese to enjoy later on your ride.

From Perry’s, pedal west on Commercial Street (it’s here where the street curves in front of the watchful eye of the William Shakespeare bust in the second-floor window of 112 Commercial Street). Venturing into the West End, you’ll find several houses with a blue plaque showing a white house on a barge: These homes were originally built on Long Point, at the very tip of Cape Cod, but were later floated to firmer ground across the harbor. 

On the left side of Commercial, look for Captain Jack’s Wharf, a collection of rustic overwater cabins that are available for overnight stays from late May through mid-October. Tennessee Williams is said to have worked on The Glass Menagerie and A Streetcar Named Desire while staying here in the 1940s.

Keep cycling west, and eventually you’ll spy the sprawling, gray-shingled Land’s End Inn perched atop a hill on your right. (Psst: If you’re feeling thirsty on your way home later, you can pop up to the inn’s grounds from 4 to 8 p.m. Fridays through Sundays for a wine or beer with panoramic views of Provincetown Harbor.)

Just up the block you’ll see the scarlet siding of The Red Inn, a highly popular restaurant for dinner and weekend brunch as well as a hotel for overnight guests. It’s easy to imagine yourself unwinding on an Adirondack rocking chair on the inn’s waterfront back deck — perhaps with a tea-tini made with Earl Grey–infused Plymouth Gin.

You’ll eventually hit a rotary at the western end of Commercial Street. This is where you’ll see folks walking across the historic granite breakwater that extends to Long Point and Wood End Light. Want to join them? Just be mindful of your timing if you want to stay dry, as high tide can splash over the breakwater.

Beyond the breakwater, Commercial Street curves into Province Lands Road. The mix of marsh and dunes on the left signals your entrance into the Cape Cod National Seashore, where you’re now bound for some of Ptown’s most popular beaches.

On your left, look for Herring Cove Beach, which you can access via the Province Lands Bike Trail entrance off Province Lands Road. From there, you can either stick around Herring Cove for some fun in the sun or keep pedaling through the parking lot, where the bike trail continues north on a scenic, winding route through the National Seashore and ultimately to Race Point Beach. Both Herring Cove and Race Point are gorgeous, popular stretches of sand. Race Point’s more direct exposure to the Atlantic Ocean means bigger waves and wind gusts compared to the bay-facing Herring Cove; it also means more spectacular sunsets.

Once you’ve had enough beach time, return via the Province Lands Bike Trail and Province Lands Road back to Commercial Street. After all, it’s almost tea-tini time.

Planning Your Trip

Lodging ideas: Provincetown has a diverse collection of inns, B&Bs, and hotels to suit any budget, with most properties offering lower rates during the shoulder seasons. Among the options are the stylish Salt House Inn, built from 19th-century cottages that once housed salt miners; the beachside retro-style Harbor Hotel; the luxury-minded small resort The Brass Key Guesthouse and its sister property, The Crowne Pointe Hotel & Spa; and the landmark Pilgrim House Inn, which offers a lively stay filled with on-site dining and entertainment.

• For more lodging inspiration, visit the Provincetown Office of Tourism’s “Where to Stay” listings.

Walking tours: Discover more than a dozen downtown highlights — including details on Ptown’s landmark cultural festivals — in the Provincetown Cultural District map. History buffs, meanwhile, will want to spend some time planning their must-see stops on the Historic Provincetown Walking Tour map, which spotlights some 50 (!) points of local interest.

For more information: The Provincetown Office of Tourism is the essential resource for visitors, with local advice on events and activities, gallery and restaurant listings, and more. Start planning your perfect Provincetown escape at ptowntourism.com